PYRIDOXAL PHOSPHATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10NO6P.H2O
Molecular Weight	265.1571
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CC1=C(O)C(C=O)=C(COP(O)(O)=O)C=N1

InChI

InChIKey=CEEQUQSGVRRXQI-UHFFFAOYSA-N

InChI=1S/C8H10NO6P.H2O/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14;/h2-3,11H,4H2,1H3,(H2,12,13,14);1H2

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00114
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20532028 | https://clinicaltrials.gov/ct2/show/NCT00157729 | https://clinicaltrials.gov/ct2/show/NCT00917293 | https://www.ncbi.nlm.nih.gov/pubmed/12213051 | https://www.ncbi.nlm.nih.gov/pubmed/23510563

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P) is a coenzyme, the active form of vitamin B6. Pyridoxal 5′-phosphate (PLP) is used as a cofactor for a wide range of enzymes including mitochondrial cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM), and d-serine dehydratase. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates. PLP acts as a coenzyme in all transamination reactions, in various beta-elimination reactions, in the condensation reaction in heme synthesis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
P2X purinoceptor 1 10 Target ID: CHEMBL2530 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12213051	Antagonist 2778	3000.0 nM [EC50]
P2X purinoceptor 2 6 Target ID: CHEMBL2531 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12213051	Antagonist 2778	39500.0 nM [EC50]
P2X purinoceptor 1 10 Target ID: CHEMBL2094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23510563	Antagonist 2778	10.0 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Tardive dyskinesia 15 Sources: https://clinicaltrials.gov/ct2/show/NCT00917293	Primary	Phase II 1132	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://clinicaltrials.gov/ct2/show/NCT00157729	Primary	Phase II 1132	Unknown Approved Use Unknown
Metabolic syndrome 32 Sources: https://clinicaltrials.gov/ct2/show/NCT00157729	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Correlation of MRI and CT findings with histopathology in hepatic angiomyolipoma.	2001	11519547
Testing the tyrosine/catecholamine hypothesis of oral contraceptive-induced psychological side-effects: a controlled study on triphasil.	2001	11423701
The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.	2001 Apr	11345696
Renal microvascular effects of P2 receptor stimulation.	2001 Apr	11339210
Lack of catalytic activity of a murine mRNA cytoplasmic serine hydroxymethyltransferase splice variant: evidence against alternative splicing as a regulatory mechanism.	2001 Apr 24	11305908
Crystal structure of maltose phosphorylase from Lactobacillus brevis: unexpected evolutionary relationship with glucoamylases.	2001 Aug	11587643
Production of pyridoxal phosphate by a mutant strain of Schizosaccharomyces pombe.	2001 Aug	11577719
Clinical and cost effectiveness of a new hepatocellular MRI contrast agent, mangafodipir trisodium, in the preoperative assessment of liver resectability.	2001 Aug	11508618
A bioinformatical approach suggests the function of the autoimmune hepatitis target antigen soluble liver antigen/liver pancreas.	2001 Aug	11481605
Structure of human cystathionine beta-synthase: a unique pyridoxal 5'-phosphate-dependent heme protein.	2001 Aug 1	11483494
P2X3 knock-out mice reveal a major sensory role for urothelially released ATP.	2001 Aug 1	11466438
Crystal structure of histidinol phosphate aminotransferase (HisC) from Escherichia coli, and its covalent complex with pyridoxal-5'-phosphate and l-histidinol phosphate.	2001 Aug 24	11518529
Inhibitory effect of glycation on catalytic activity of alanine aminotransferase.	2001 Feb	11330835
Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X1 receptors.	2001 Feb 1	11462975
Inhibitors of advanced glycation end product-associated protein cross-linking.	2001 Feb 14	11341999
Metal ion inhibition of nonenzymatic pyridoxal phosphate catalyzed decarboxylation and transamination.	2001 Jan 17	11456503
Serum cystatin C is an independent predictor of total homocysteine levels in stable Korean renal transplant recipients with normal serum creatinine.	2001 Jul	11466665
Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy.	2001 Jul 1	11543957
The human cDNA for a homologue of the plant enzyme 1-aminocyclopropane-1-carboxylate synthase encodes a protein lacking that activity.	2001 Jul 11	11470512
X-ray structure of Escherichia coli pyridoxine 5'-phosphate oxidase complexed with pyridoxal 5'-phosphate at 2.0 A resolution.	2001 Jul 20	11453690
Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues.	2001 Jun	11575573
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus).	2001 Jun	11423336
Stimulation of P2 receptors in the ventral tegmental area enhances dopaminergic mechanisms in vivo.	2001 Jun	11406200
Cassette mutagenesis of lysine 130 of human glutamate dehydrogenase. An essential residue in catalysis.	2001 Jun	11389722
Sensitivity to meat protein intake and hyperoxaluria in idiopathic calcium stone formers.	2001 Jun	11380831
PPADS, an ATP antagonist, attenuates the effects of a moderately intense sound on cochlear mechanics.	2001 Jun	11377878
Dephosphorylation of MnDPDP and related compounds by acid and alkaline phosphatase.	2001 Jun	11377042
ATP affects both axons and Schwann cells of unmyelinated C fibres.	2001 Jun	11376907
Low circulating vitamin B(6) is associated with elevation of the inflammation marker C-reactive protein independently of plasma homocysteine levels.	2001 Jun 12	11401933
Role of endogenous ATP at the incision area in a rat model of postoperative pain.	2001 Jun 13	11409742
Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation.	2001 Jun 22	11430931
Homocyst(e)ine metabolism in hemodialysis patients treated with vitamins B6, B12 and folate.	2001 Mar	11426667
Crystal structure of threonine synthase from Arabidopsis thaliana.	2001 Mar	11344332
Adult hypophosphatasia. Current aspects.	2001 Mar	11324927
A placebo-controlled, double-blind, randomised trial of magnesium-pyridoxal-5'-phosphate-glutamate for hypercholesterolaemia and other clinical-chemical risk factors of cardiovascular disease in a primary care setting.	2001 Mar	11317472
Effect of phosphate on stability of pyridoxal in the presence of lysine.	2001 Mar	11312896
Intracellular signaling pathways involved in acetaldehyde-induced collagen and fibronectin gene expression in human hepatic stellate cells.	2001 May	11343241
Three-dimensional structure of 2-amino-3-ketobutyrate CoA ligase from Escherichia coli complexed with a PLP-substrate intermediate: inferred reaction mechanism.	2001 May 1	11318637
Molecular cloning and functional expression of Xenopus laevis oocyte ATP-activated P2X4 channels.	2001 May 2	11334629
Accelerated functional recovery after neuronal injury by P2 receptor blockade.	2001 May 25	11408042
ABA3 is a molybdenum cofactor sulfurase required for activation of aldehyde oxidase and xanthine dehydrogenase in Arabidopsis thaliana.	2001 Nov 2	11553608
Cloning, sequencing, heterologous expression, purification, and characterization of adenosylcobalamin-dependent D-ornithine aminomutase from Clostridium sticklandii.	2001 Nov 30	11577113
COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk.	2001 Oct	11577006
Crystal structures of 1-aminocyclopropane-1-carboxylate (ACC) synthase in complex with aminoethoxyvinylglycine and pyridoxal-5'-phosphate provide new insight into catalytic mechanisms.	2001 Oct 12	11431475
P2Y(AC)(-)-receptor agonists enhance the proliferation of rat C6 glioma cells through activation of the p42/44 mitogen-activated protein kinase.	2001 Sep	11564659
Cloning and characterization of a functional P2X receptor from larval bullfrog skin.	2001 Sep	11502572
ATP P2X receptor-mediated enhancement of glutamate release and evoked EPSCs in dorsal horn neurons of the rat spinal cord.	2001 Sep 1	11517241
Properties and interaction of heterologously expressed glutamate decarboxylase isoenzymes GAD(65kDa) and GAD(67kDa) from human brain with ginkgotoxin and its 5'-phosphate.	2001 Sep 13	11543686
Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems.	2001 Sep 17	11570704
Plants synthesize ethanolamine by direct decarboxylation of serine using a pyridoxal phosphate enzyme.	2001 Sep 21	11461929

Patents

Sample Use Guides

In Vivo Use Guide

500 mgs po bid for 12 weeks.

Route of Administration: Oral

In Vitro Use Guide

Male Wistar rat (body weight -200 g) was sacrificed by bleeding from the right femoral artery under diethyl ether anesthesia. A thoracic aorta was removed and washed with RPMI 1640 medium to avoid contamination with blood. It was then turned inside out, and cut into short segments of about 1-1.5 mm. Each aortic segment was placed in the center of a well on a 6-well culture plate and covered with 0.5 ml of gel matrix solution reconstituted as described. The solution was allowed to gel at 37°C for 20 min, and then overlaid with 2 ml of RPMI 1640 medium (Gibco, New York, USA) containing 1% of ITS+ (Becton Dickinson Labware, MA, USA). PLP (Pyridoxal phosphate ) was reconstituted in phosphate buffered saline and added on day 1. Incubation was carried out for 10 days in a fully humidified system of 5% C02 in the air at 37°C. The medium was changed on day 7 of the culture.

Name

Type

Language

PYRIDOXAL PHOSPHATE

Common Name

English

PYRIDOXAL PHOSPHATE [MART.]

Common Name

English

PYRIDOXAL PHOSPHATE HYDRATE

Common Name

English

Pyridoxal 5-phosphate monohydrate [WHO-DD]

Common Name

English

PYRIDOXAL PHOSPHATE MONOHYDRATE

Common Name

English

3-HYDROXY-2-METHYL-5-((PHOSPHONOXY)METHYL)-4-PYRIDINECARBOXALDEHYDE HYDRATE

Common Name

English

PYRIDOXAL 5'-PHOSPHATE MONOHYDRATE

Common Name

English

PYRIDOXAL PHOSPHATE HYDRATE [JAN]

Common Name

English

4-PYRIDINECARBOXALDEHYDE, 3-HYDROXY-2-METHYL-5-((PHOSPHONOOXY)METHYL)-, HYDRATE (1:1)

Systematic Name

English

PYRIDOXAL 5-PHOSPHATE MONOHYDRATE

Common Name

English

Classification Tree Code System Code

LOINC

75056-2